


Dean's good boy and pretty princess

by Cagedandfree



Series: Good boys for Dean [3]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Bottom Castiel, Bottom Sam, Butt Plugs, Caring Dean, Castiel is Dean's good boy, Castiel is a Sweetheart, Cock Cages, Cock Warming, Crossdressing, Crossdressing Sam, Daddy Issues, Daddy Kink, Dean is a Sweetheart, Destiel - Freeform, Dom Dean, Dom/sub, Emotional Hurt/Comfort, Enemas, Face-Fucking, Feminization, I'll add more when I think, Light Dom/sub, M/M, Nipple Pumps, Panty Kink, Praise Kink, Pretty princess Sam, Prostate Massage, Protective Dean Winchester, Rimming, Sam In Panties, Sam in Makeup, Sam is Dean's good girl, Sastiel - Freeform, Shaving, Shower Sex, Spanking, Sub Sam, Switch Castiel, Top Dean, Wincest - Freeform, cock cage with sound, piss drinking
Language: English
Status: Completed
Published: 2018-01-09
Updated: 2018-01-14
Packaged: 2019-03-02 19:47:12
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 17
Words: 12,217
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13325217
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: the third installment.Dean takes Sam home to be with Catiel and the three form a special relationship .Read the tags.





	1. Chapter 1

**Author's Note:**

> My third story in a week, I can't believe it!  
> Comment, kudos.

Castiel and Sam sat on the couch. Dean was in a chair sitting across from them. He smiled at both the men. Sam was nervous and Castiel reached over and held the younger man’s hand. Sam blushed, but looked at Cas and smiled a bit.

“Sam, we’re very happy to have you here with us.” Castiel said.

“He’s right. We’re very proud of you, Sammy” Dean said and Sam nodded. “Now, Sam is very open with our relationship and what you do for me.” Sam squeezed Castiel’s hand. 

Dean had talked to Castiel, saying that Sam just needs comfort and care more than anything. Castiel was happy that Sam had been brave enough to move it. He was always nervous with his kink, but if Sam can be open, then so can Castiel. 

“When Sam is my pretty princess, he addresses me as daddy, don’t you?” Dean smiled softly. 

“Yes” Sam whispered.

“Castiel, when you are wearing the cage all day, I would like for you to call me sir.” Castiel nodded. “Sammy, would you like to be my pretty princess, 24/7?”

“With the exception of working a case.”

“Of course. In public, all of this stops. Except if I have to use the bathroom” Dean said looking at Castiel who smiled and nodded. “You are both my subs, however, Castiel is a switch, aren’t you baby?” 

“Yes.” Castiel smiled.

“Yo-you dom…” Sam trailed off looking at Dean.

“No sweet boy. You need a lot of care, a lot of love. Castiel and I were wondering if you wanted to be his baby girl.” Sam looked shocked, at Castiel with pleading eyes. Cas cupped Sam’s cheek.

“Would you like that Sam?” Castiel asked and he nodded. Castiel placed a gentle kiss on his lips.

“What would you like me to call you?” Sam whispered. He felt the couch dip a bit and Dean sat by Sam, rubbing a hand on his back. 

“Whatever you’re comfortable with. However, when I’m wearing my cage all day, then you are both subs.” Sam nodded. Dean placed a kiss on the back of Sam’s neck. 

“Sam, if at any point, you want to wear your regular clothes, you just let us know. This is to make you feel safe and loved. We want what’s best for you.” Sam nodded.

“Castiel, I would like to just call you by your name…for now.” Sam said slowly.

“As you wish.” He smiled.

“I-I would like to. I would like to be a pretty princess now.” Sam said. Both men wrapped their arms around Sam.

“You go get ready; I’ll be there in a minute” Dean whispered and Sam stood up and left. Dean leaned over and kissed Castiel.

“Are you okay with that, baby? When I have you locked up, you call me sir?” 

“Yes, Dean. That is very okay.” Castiel smirked. 

“Okay. Now, you’ll be my good boy and drink my pee, but the sir stuff will be in a few days. Just want our girl to be comfortable.” Castiel wrapped his arms around Dean’s neck and kissed his lips.

“I like the sound of that. Our girl.” 

“And you’re really okay with this?” Dean asked, cupping Castiel’s cheek.

“Yes. The stories you have shared about your past, I’m glad that your brother has something that makes him feel safe.” Dean kissed Castiel.

“Are you ready to see how pretty he looks?” 

“I’ve been wanting to see since you told me about it. I’m so excited.” The older man beamed. 

“I’ll be right back.” 

Dean knocked lightly on Sam’s bedroom door.

“Sweetheart?” Sam opened the door. Dean saw that he was naked. Sam turned around and showed Dean the plug in his ass. “Good girl”

“Can you put the cage on me, daddy?”

“Of course, princess. On the bed.” Dean had gloves in his pocket and put them on. Sam lay on the bed and Dean lightly rubbed Sam’s balls. “Castiel can’t wait to see how pretty you are.” 

“Wh-what are you doing?” Sam whispered.

“You said you had a tough time getting hard, princess. I just want to stimulate you before I put the cage on. I’m going to do this every time I put the cage on.”

“Okay.” Sam said.

“Good girl” Dean reached over and put the cage on Sam. 

Sam stood up while Dean took the gloves off. Dean watched as his princess put the panties on, stockings, heels and gloves. 

“Can you put the lipstick on?” 

“Sure thing, pretty girl” 

Once Sam was dressed, Dean took his hand and walked with him to the library. Castiel smiled to when he heard the clicking of the heels. Dean walked in and so did Sam. Castiel smiled wide when he saw Sam.

“Wow.” He said.

“Castiel, do you think I’m pretty?” Sam whimpered and Castiel got up and walked over to him, stroked his cheek.

“I think you’re the prettiest baby girl, I have ever seen.” 

“Really?”

“Uh huh. You’re a pretty girl for your daddy, aren’t you?” Sam nodded.

“Princess, I want you to dance for daddy and Cas.” Dean instructed.

“Yes, ddaddy. I would like that.” 

Dean and Castiel sat in chairs and watched as Sam started to dance for them.


	2. Chapter 2

“Baby girl” Castiel spoke. Sam looked up at him.

“Yes” Sam swallowed.

“Can you come sit on my lap? I want to hold you.” Dean watched happily as Sam straddled Castiel. Sam rested his head on Castiel’s shoulder and the blue eyed man wrapped his arms around him.

“Princess, can daddy ask a favor of you?” Dean spoke up. Sam looked over at Dean. “Would it be possible, before if we tried to stimulate you a bit more? Try to get you nice and hard, to see how long you can hold it?” Sam whimpered, but nodded. Dean got up and walked over, to stroke Sam’s hair.

“Yeah, sweetie? Daddy and I can do that?” Castiel whispered.

“Yes.” 

“Good girl.” Dean praised. 

Sam relaxed against the touches of the two older men. A little while later Dean had to go to the bathroom.

“Princess, I need my good boy for a moment.” Dean said undoing his pants. Sam stood up.

“Can I do something for you?” Sam asked his brother.

“You can dance for me. I love seeing my pretty girl dance."

“Yes, daddy.” Sam said. 

With Dean’s eyes locked on Sam, Castiel knelt by Dean and took his cock in his mouth. While Dean peed, he ran a hand through Castiel’s hand. 

“Touch your face princess, feel the gloves against your skin.” Dean instructed. 

Sam ran the gloves over his cheek and one down his neck. Lips parting. Castiel licked Dean’s tip and looked up at him.

“Thank you, baby” Dean said with a wink.

“You’re welcome sir” Castiel smiled.

“Sweetheart, you are an incredible dancer. You like the feel of the gloves?” Dean asked standing up and doing his pants up. Castiel went back to research.

“Yes, I love the way they feel and look.” Dean placed a hand on the back of Sam’s head and Sam stopped moving. Dean placed a kiss on the younger man’s lips. 

“You’re beautiful. You’re such a pretty girl for me.” 

“Do you want to sit back on my lap, or keep dancing?” Castiel asked.

“I want to keep dancing. I want to show you how pretty I can be.” Sam said.

“Good girl” Dean praised.

When it was time for bed, Dean helped Sam get in his nightgown and new stockings. When they walked into the living room, Sam gave a twirl. 

“Would you look at our girl” Dean said and Sam blushed. 

“So beautiful.” Castiel smiled. 

“Now princess, we’re going to try to get you hard” Dean instructed.

Yes daddy” he whispered.

Castiel sat on the couch. Dean pulled the panites off of Sam, the babydoll nightgown almost covering his ass.

“Sit on my lap, baby girl. I’m going to keep your legs open” Castiel said. 

Sam nodded and sat on Castiel’s lap. Cas spread his legs making Sam’s open. Dean pulled up a chair and don latex gloves. Castiel stroked Sam’s hair, arm wrapping around his waist.

“Close your eyes princess, just breathe and relax. This is a safe place.” Dean whispered and Sam did. 

Sam gasped when he felt Dean take him in his hands. Lying Sam’s penis in one hand, with his other hand Dean started to stroke Sam. He nodded at Castiel.

“You are such a pretty girl. Such a good girl for your daddy” Castiel whispered, making Sam shudder. “You are so beautiful and loved. You’re special and perfect. A perfect baby girl for me.” Sam’s cock twitched a bit in Dean’s hand. “Such a pretty girl” Castiel lightly bit Sam’s earlobe and Sam groaned. 

After five minutes, Sam was a half erect. He opened his eyes and looked at Dean. Dean looked at him sympathetically. Sam started to cry and Castiel soothed him.

“I’m sorry. I’m a disappointment.” Sam whimpered.

“No. Oh princess, you’re not a disappointment.” Dean said, his heart breaking a bit. Dean Took the gloves off and Castiel moved Sam so he could cradled him. Dean sat with Sam’s back to him. 

“You did such a good job. You got half erect, that’s amazing. You are amazing” Castiel whispered. 

“I’m a failure. I’m a bad girl.” Sam whimpered. 

“Noo. You are not a bad girl. You’re a good girl.” Dean said wrapping his arms around Sam and placing a kiss on the top of his head. 

“See, you’re still hard.” Casitel observed. Sam nodded. “That’s very good, sweetie.” 

“I’m not a disappointment?” He turned to look at Dean and Dean kissed his lips.

“Never. Now, I’m going to get some ice to bring that down. Then” He looked at Castiel. “I’m going to get you both ready for bed.” Castiel nodded before placing a kiss on Sam’s forehead.


	3. Chapter 3

Castiel was naked except for the cock cage. Dean was also naked, Castiel was warming Dean’s cock while Sam was dancing.

“I have such a good boy.” Dean said stroking Castiel’s head. “Princess, come here please.” Dean said and 

“Yes daddy” Sam said walking over. Dean ran his fingers over Sam’s pantie covered ass. 

“How’s the new plug, sweetheart?”

“It’s stretching me nicely” Sam whispered.

“Good girl. Baby boy, you may stop warming my cock.” Dean said and Castiel slowly removed Dean from his mouth. 

“Did I do good, sir?” Castiel asked.

“Yes you did. So good for me. I’m going to take your cage off now. You have some to meet with the cornier.”

“Yes sir.” Castiel stood up and Dean turned his attention to Sam and cupped his cheek.

“Princess, do some research, while I get my good boy ready.” 

“Yes, daddy.”

In the bedroom Dean took Castiel’s cage off. He kissed his boyfriend and gave a squeeze to Castiel’s cock.

“Ah!” Castiel gasped.

“You were so good for me, baby. Such a good boy. I’m going to let you cum tonight. Okay?” 

“Yes, Dean.” 

“Take a cold shower. I love you.”

“I love you too.” 

When Castiel left, Dean, now dressed crouched in front of Sam. 

“Hey, pretty princess.” He cooed and Sam blushed. “I know somethings been on your mind.”

“Yes.” Sam whispered.

“What is it, sweetheart? All you have to do is ask.” Dean sat on the couch and Sam got on his knees, placing his hands on Dean’s thighs. Dean, cupped Sam’s cheek.

“I want you to spank me, daddy. I want you to give me praises, while spanking me.” Dean rubbed a thumb on Sam’s cheek. He placed a kiss to his lips. 

“I will spank you, princess, if you’ll do something for me.” Dean whispered.

“Oh yes. Whatever you want.” Sam gripped Dean’s thighs.

“Tonight, I will be fucking Castiel. Since you’re his baby girl, I thought it would be awfully nice to have him fuck your pretty, pretty mouth.” Sam whimpered. “Would you like that, princess? If it’s too much, you let me know.”

“I want to be a good girl for him. Please, let Castiel fuck my pretty mouth.” Dean kissed Sam’s forehead.

“Can I ask one more thing of you?” Dean whispered.

“Anything, daddy.”

“Daddy would like to put your hair in pigtails. You’re already very beautiful, but I think my good girl should be in pigtails.” Dean saw a flash of excitement in Sam’s eyes. Sam nodded. “Yeah?”

“Yes, daddy. Please. Make me the prettiest princess.” 

Once Sam’s hair was in pigtails, Dean grabbed the lipstick and opened it. It applied more and led him over to the bed. He rubbed his hands up and down Sam’s gloved arms. 

“Are you ready, princess?” Sam nodded.

“Yes, daddy.”

Dean sat on the bed and patted his lap. Sam went across him. Hands touching the floor. Dean rubbed a hand on the back of Sam’s thigh. Sam lowered his head when he felt Dean place a hand on his lower back. Three light smacks came to his butt.

Smack. Smack. Smack.

“You like that, princess?” Smack. Smack. Smack. “You’re a good girl. Such a good girl for daddy.” Dean kept lightly spanking his brothers, with some sharper smacks in between. “You look so pretty like this. Bent over my knee. You’re a pretty princess. A very pretty princess.” Dean started to massage Sam’s butt a bit before returning to spank him. “You make daddy proud. So proud sweetheart. You’re a good girl. So good for me and Castiel. Do you think you’re pretty, princess?” when Sam didn’t answer Dean give a sharper smack making Sam gasp.

“Yes. Yes. I think I’m very pretty.” Sam answered. Softer spanks came to his ass.

“Do you know how amazing you look in pigtails? Yeah, daddy likes his girl in pigtails. That’s how you’re going to be from now on. My pretty princess.” Dean rubbed Sam’s butt, giving it squeezes. “How was that, sweetheart?”

“That was perfect, daddy” Sam said. Dean helped Sam up. Sam went to the ground, to kneel in front of Dean. Sam looked away when Dean stroked the back of his hand on Sam’s cheek.

“What is it, princess?”

“Co-could you…could you sometimes add Sammy to the end of pretty princess?” Dean smiled, turning Sam’s face to look at him.

“Are you my pretty princess, Sammy?” Dean cooed and Sam blushed. 

“Yes, daddy.”

“Yes you are.”


	4. Chapter 4

Dean was moving slow inside Castiel, while Sam’s tongue worked around Castiel’s cock.

“Mmm, baby girl, you’re really good at that” Castiel praised Sam.

“You like the pigtails?” Dean asked

“I do. Very pretty.” Sam smiled around Castiel’s cock. 

Sam was kneeling on the ground and Castiel’s hands were on the bed, balancing himself, while Dean’s hand was in his hair and the other arm wrapped around his waist. 

“Harder, Dean” Castiel said and Dean happily obliged. 

Dean started grunting and Castiel was panting. One of Castiel’s hand found its way back to Sam’s head and he started to slowly fuck his mouth.

“Hnn” Sam whined. 

“You okay princess?” Dean asked, slowing down. Sam nodded. Pretty soon both men came. Sam quickly got out of the way while Dean and Cas collapsed on the bed.

“Fuck baby, that was amazing” Dean whispered to Castiel. “Princess, come here. Sam stood up and walked over, lipstick smeared. “Did you enjoy that?”

“Yes daddy. I enjoyed being a good girl for Castiel.” Castiel reached out and grabbed Sam’s gloved hand. 

“You were very good. Such a good baby girl.” Dean pulled out of Castiel. 

“sweetheart, would you like to join us in the shower?” Dean asked Sam and he nodded.

Dean and Castiel got Sam out of the panties, gloves fishnet stockings and heels. Dean took off Sam’s cock cage and pulled the plug out. 

“Daddy?” Sam whispered.

“What is it pretty girl.”

“Would it be possible if I didn’t wear my cage tomorrow for the day?” Dean kissed his brothers lips and nodded.

“Okay.” 

Once the boys were all showered, Dean caged Castiel and went to the bathroom while Sam dried off and got in his nightwear. Dean attached the cage, but not the plug, not at night and pulled Sam’s panties back up. Castiel slipped his pajama pants on.

The three of them climbed into bed. Sam’s back was pressed against Dean’s and he was facing Castiel. Castiel stroked his hair.  
“Baby girl, can I ask you something.” Castiel whispered. Sam nodded. I was curious as to why you wanted to be called a girl. Do you feel like you’re in the wrong body? Do you feel like a girl?” 

“No. It’s not that at all.” 

“What is it princess?” Dean whispered, pressing a kiss to the back of the younger man’s head.

“My whole life…dad he told me a was a disappointment. I stupid boy, dumb boy. That I couldn’t do anything right.” His voice broke and Dean pulled him close. Castiel kissed his forehead. “So, that’s why I do this. So I won’t have to have his voice in my head. I kept thinking maybe it would have been better if I was a girl. But…again it’s not that I think that I am. Just…” 

“Thank you for sharing that, sweetie” Castiel said, letting him know that he understood. After a moment Dean spoke softly.

“You’re my pretty princess, Sammy. You’re my pretty girl.”

“Thank you, daddy.” Sam whispered. 

“Get some rest, sweetie.” Castiel whispered and Sam closed his eyes.


	5. Chapter 5

There was a new case and they had to travel for it. Dean got the bag ready for his subs. He walked into the living room and saw Castiel holding Sam. His hair now in pigtails.

“Princess?” Dean asked, rubbing a hand on his back.

“Yes, daddy” Sam looked at him.

“We’re going to be in the car all day long. We will only be stopping for meals.” Sam looked up at Dean. “Do you want to be my pretty princess, Sammy? Do you want to wear your pretty panties and stockings under your clothes?”

“Can I?” Sam looked at Dean and then Castiel. 

“Baby girl, we just want you to be happy.” Castiel said kissing his forehead.

“Okay. But no cage.”

“No cage, sweetheart” Dean smiled, and tapped against the plug in Sam’s ass. Sam gasped. “But this goes in. And you will be wearing your heels in the car, but can change into your regular shoes when we go out.” Dean said. 

“Will Castiel be your good boy?” Sam looked at both men wide eye. Castiel stroked Sam’s cheek.

“Sweetie, I will be drinking from bottles in the car ride….as for the cage.” Castiel looked up at Dean who shook his head.

“Castiel will not be in a cage either.” Dean clarified.

“Okay” Sam smiled. “What about the gloves, daddy?”

“You will be in a t-shirt, so you can wear them in the car.” Sam smiled and nodded. “Good girl.”

Sam stood up from Castiel’s lap and go on his knees. The boys didn’t tell him to ask his questions like this, it was something he decided himself and if that’s what he wanted, then who were they to question it.

“Please let me be the prettiest princess tomorrow. Put my hair in pigtails and paint my lips. I want to feel so pretty for our trip.” Dean crouched down and cupped Sam’s cheek placing a kiss on his lips. 

“Whatever you want.” He smiled.

In the morning Dean got the cages off the boys and washed them. Castiel stroked Sam’s hair and held him tight to him. When Dean came back he put latex gloves on and grabbed the bigger plug. Sam whimpered.

“Baby girl, is that okay?” Castiel and Sam nodded.

Sam rolled on his elbows and knees. Castiel stroked his hair while Dean squirted the lube in Sam’s hole. He worked a finger in before getting more lube and working a second finger in. Castiel blushed, feeling himself get hard. Dean smirked at him and then worked a third finger in.

“Relax for me princess, you’re a good girl” Dean praised Sam. 

Once the plug was in, Sam stood up and Dean took the gloves off, he looked at Castiel who was a hard.

“Be a good boy and get dressed” Dean said and Castiel nodded. 

“Okay, sweetheart. Let’s get you all ready for today. I have your regular clothes ready, but first, be a good girl and get your panties, gloves and stockings on.” He kissed Sam gently.

“Then daddy will make me look pretty” Sam whispered and Dean smiled.

“Yes, princess. Daddy will make you so pretty.” 

Castiel came back dressed once Sam had all his princess clothes on. Dean helped Sam step into his jeans and Den did them up. Castiel held Sam’s hand as he stepped into the heels. Sam put the t-shirt on and looked down at himself.

“I don’t feel very pretty” he whimpered and Castiel hugged him.

“But you are, baby girl. You are so pretty. Even like this.”

“You are such a beautiful girl, Sammy” Dean cooed. 

Sam nodded and sat on the chair. Dean placed Sam’s hair in pigtails and Castiel put the lipstick on. 

“There, that’s better.” Castiel said.

“Princess, daddy knows you don’t like this, but tonight, I promise, we’ll make it up to you.” Dean said and Sam smiled.


	6. Chapter 6

Castiel and Sam went to the car, Sam in the back so he could stretch out. 

“Castiel?” Sam asked.

“Yes, baby girl”

“Are you still hard?” 

“Yes, sweetie.” Castiel looked at the younger Winchester and smiled sweetly. Dean came over to Castiel’s side of the car and smiled when he saw that Castiel had his pants undone. 

“Good boy.” Dean said, placing the ice pack on his hard on. Castiel gasped. “Hey princess” Dean cooed. Sam blushed and waved.

They drove and finally stopped for lunch. Dean got in the back with Sam and helped him change his shoes and wipe the lipstick off and take his hair out. Sam whimpered.

“You are such a pretty girl, such a pretty princess for me. But we’re going in public, okay?” Dean said and Sam nodded. Dean placed a light kiss on Sam’s lips. “Who’s my good girl?”

“I am, daddy” Sam said.

Castiel drove for a bit while they slept. When they pulled into the motel, Sam practically ran inside. Both men chuckled.

“Our girl did good today” Castiel said and Dean smiled.

“So did you, baby. You’re my good boy.” Dean kissed Castiel and they walked in, seeing Sam was out of his regular clothes.

“It’s not that late, baby girl. Would you like your surprise from daddy?” Castiel asked.

“Yes, Castiel. But…I would like to be in my nightgown.” Sam said and Dean smiled.

“Let me get your plug out and your cage on.” Dean said.

Once Sam was changed, Dean had Sam sit at the table. Castiel saw Dean put Sam’s hair back in pigtails. He noticed that Sam was still wearing his satin gloves.

“You still have the gloves on” Castiel said.

“Yes, Castiel. Daddy wants me to dance for him, so I will keep them on for that.” Sam said. 

“Very good.” Castiel smiled at Dean and then raised an eyebrow when Dean pulled pink ribbons out.

“Princess, daddy is sorry you didn’t feel very pretty today. Would you like to be the prettiest princess ever? No questions asked?” Sam, wide eye, nodded. “Then daddy is going to get you all dolled up. First he’s going to put pretty pink bows in your hair, would you like that?”

“Yes, daddy” Sam whispered blushing. Dean placed the ribbons in and then stroked Sam’s cheek.

“Daddy was thinking of putting makeup on his princess.”

“More than lipstick?” Sam gasped.

“Would that be alright?” Castiel asked. Sam wrapped his arms around Dean’s waist and nodded.

“Good girl.” Dean smiled.

He grabbed the makeup bag and told Sam to close his eyes. Dean applied the eyeshadow. He then applied mascara, blush and last but not least, the bright red lipstick. Sam went and looked in the mirror. He gasped and both men looked over.

“I thought I was pretty before, but I’m beautiful.”

“Yeah, you like it, sweetheart.”

“Oh yes. I’m the prettiest princess.”

“Yes you are, baby girl.” 

“Will my pretty girl dance for me?” Dean asked, sitting down. 

“Yes, daddy” 

Dean and Castiel watched in awe as Sam started to dance. He looked so beautiful with his hair and makeup. Fifteen minutes later, Sam stopped dancing at knelt on the ground.

“What do you want, sweetheart” Dean smiled sweetly.

“I’m a pretty girl who wants to be spanked” Sam answered. 

“Okay, princess, but after we’re going to stimulate you.” Dean said cupping the younger man’s cheek.

“Yes, daddy.” Sam stood up and Dean called Castiel over. 

“You’re going to lie on the bed and get a spanking from both of us.” Dean said and Sam smiled, nodding.

Castiel placed a pillow under Sam’s hips. Both men rubbed a hand up and down Sam’s legs. Dean placed a gentle smack on Sam’s ass.

“You’re a pretty princess, Sammy” Dean said. Castiel smacked Sam’s butt.

“Such a good baby girl” Castiel praised. The boys took turns spanking.

“You look so beautiful with your makeup. I think that’s how daddy wants his girl from now on” Dean said.  
“And your hair in the pretty bows. Such a beautiful girl, sweetie” Castiel said.

“We love when you dance for us.” Dean continued.

“Your nightwear is stunning on you” Castiel added.

“You’re the prettiest girl, I ever laid eyes on. Sammy, you’re the prettiest princess in the whole wide world.”

“Daddy, Castiel” Sam whimpered.

“What is it?” Dean soothed. Both men now rubbing and squeezing Sam’s ass. 

“I-I would like for you to try and stimulate me now.” Castiel rubbed down his legs.

“Okay, princess. Castiel is going to rub your cock and daddy is going to massage your prostate.”

“Yes, daddy” Sam whispered.

**Notes for the Chapter:**

> I hope you guys are enjoying this.   
> I would love to know what you would like to see next. There will be more Dean and Castiel soon.
> 
> *Still secretly wants someone to do fan art of this story.*


	7. Chapter 7

“Good girl. Good girl. I’m going to insert my fingers now.” Dean said.

Sam was on the floor on his elbows and knees, panties by his ankles. Dean and Castiel were kneeling beside him, both in latex gloves. Castiel was stroking Sam’s cock. Dean squirted some lube into Sam’s ass hole. He squirted some on his gloved fingers and rubbed them together. He rubbed it against Sam’s hole and inserted them. 

“Nah” Sam gasped.

“Baby girl, you’re going a good job” Castiel said feeling Sam’s cock twitch and start to grow. Dean placed a firm hand on his lower back.

“Princess, daddy is going to rub you now.” Dean warned. 

Dean rubbed against Sam’s prostate and castiel rubbed Sam’s balls. Sam’s head was down. Castiel looked at Dean, smiling and nodded.

“Sweetheart, looks like this is working.” Dean said. “Good girl.”

“Hnn. Hnn. Hn.” Sam started to pant.

“How long has hit been since you’ve cum, sweetie?” Castiel asked in a soothing voice.

“Se-seven mo-months” Sam panted out. “Ahhh, daddy. Please!” 

“Seven months? Pretty girl, you should have told us.” Dean said, rubbing still. Castiel gave a few tugs to Sam’s cock.

“So-sorry” Sam whimpered.

“Oh, you have nothing to be sorry for, baby girl” Castiel said.

“Alright princess. You’re fully erect. We’re going to take out hands away and see how long it’ll stay up.” Dean said nodding at Castiel. 

Both men removed their hands. Sam started whimpering and shaking. He rolled over on his side in the fetal position, cock sticking straight out. Dean was by his head, lifting it in his lap.

“You’re so pretty like this princess. Such a pretty girl.” Dean soothed, rubbing a hand over his brothers temple. 

Castiel put new gloves on and touched Sam’s cock. Sam let out a cry, eyes screwing such.

“Is it painful, sweetie” Castiel asked voice laced with sympathy. Sam just nodded. “I can imagine. Not being able to get hard for seven months must have been challenging.” Sam nodded.

“Princess, I know it hurts, but we need to see how long you can last before we take care of it. You are such a good girl, Sammy. So pretty like this. Face all dolled up, ribbons in your hair. You make daddy very proud.” Sam reached out a hand and Castiel took it. Dean took Sam’s other hand.

“Da-Daddy” Sam whispered.

“Yeah, sweetheart.” 

“Am I’m pretty like this? With my cock hard?”

“Princess, this is the most beautiful I have ever seen you look.” Dean whispered back. 

After ten minutes, Sam’s whimpers and painful cries were too much for the boys. Dean nodded at Castiel who stated to play with Sam’s cock.

“Hmmmm. Please. Let me cum.” Sam whimpered.

“We’re going to baby girl” Casitel assured him.

“Hold me, daddy.” 

“I will, princess. You just relax and let the feelings wash over you.”

When Sam finally came it was a howling yell. He broke into hysterical sobs. Dean held his brother tight to him while Castiel cleaned everything up. 

“you were so brave. You were a brave girl, Sammy. Such a good princess for me.” Dean praised him. 

“Dean, I don’t think the cock cage will be a good idea tonight” Castiel said, gently wiping Sam clean with a warm cloth.

“I agree.” Dean nodded.Sam clung to Dean. “Okay, sweetheart. You will not be in a cage tonight. Baby, if you don’t want to wear your tonight, you don’t have to” Dean spoke to Castiel.

“Thank you, Dean.”

Castiel pulled Sam’s panties up, earning a moan. Dean lifted Sam up in his arms and laid him down on the bed.

“Princess, Castiel is going to wipe the makeup off you’re pretty face.” Dean whispered and Sam nodded.

While Castiel wiped Sam’s face, Dean peed in a mason jar and put a straw in it. Castiel smiled, knowing that Dean wanted to hold his brother and that they needed to take care of their sub. Castiel took Sam’s gloves off and pigtails out. Dean got undressed and climbed into bed, pulling Sam close. Castiel got in his pajamas.

“Ca-Cas” Sam asked.

“He’s just getting his pajamas on and getting his warm drink.” Dean soothed.

Castiel climbed in bed with the mason jar and sipped Dean’s pee and rubbed a hand on Sam’s back.

**Notes for the Chapter:**

> Is it wrong that I really wish someone would make fan art of this? Guys...is anyone out there?


	8. Chapter 8

**Summary for the Chapter:**

> Sammy is out, so Dean and his good boy get to play

Dean walked out of the bathroom to see Sam dressed like a social worker. He sighed a bit and Dean walked over to his brother and kissed him.

“I know, Sammy. However, the little girl opened up to you more.” Sam nodded.

“I know. I’m happy she did. I will be back, a little later.” Sam smirked a bit and Dean did too.

Sam left and Dean walked into the bathroom where Castiel was holding in an enema. Cock cage on him. 

“Ple-please, sir.” Dean sat on the edge of the tub and rubbed a hand on his head. 

“Shhhh, baby boy. You’re doing good for me. Sammy is going to talk to the little girl and we’re going to have some fun.” 

“Ye-yes” Castiel nodded. 

Dean stood up and got undressed in front of him, making Castiel whimper more. Dean took the cage off and helped Castiel release and kissed him. 

“Are you going to pee in my ass, sir?”

“Mmm, baby, I have a plan for you.” 

Dean had Castiel go on the bed, hands and knees. Castiel heard Dean put on gloves and popped the lube cap. 

“Are you going to be a good boy for me?” Dean asked spreading Castiel’s ass cheeks.

“Yes, sir” he whimpered. “AH!” Castiel screamed when he felt the tip of Dean’s tongue wiggle over his hole.

“There’s a good boy.” Dean laid his tongue flat against his ass and licked up.

The noises coming from Castiel’s mouth Dean had never heard before. Dean slowly circled Castiel’s ass. He pulled back and watched his muscles contract . 

“You like that, baby?” Dean growled.

“Ye-yes sir.” The older man whimpered. 

“Do you want more? All you have to do is ask.”

“Ple-please. Sir, please. I want your tongue on my ass. I want you to eat me. Please. Please!” 

“Mmm, yeah. You want that? You want this” Dean licked it again.

“What else?”

“F-fuck me. Fuck my ass, sir. I want it, I need it.”

Dean continued to eat Castiel’s ass. When he felt Castiel was close he pulled back and rubbed a finger. He grabbed some lube and squirted it on Castiel’s ass. He moaned and let out a cry.

“Good boy. Now, you’re not going to cum until I tell you too.” Dean whispered.

Castiel panted as Dean inserted two fingers in his ass. Once Dean felt castiel and slowly slid in him. Dean took the gloves off and felt Castiel clench around him. He was dripping pre-cum.

“Aww, you’re not going to disobey me, are you?” Dean warned.

“Pl-please. I-nee-need” Castiel begged. “Sir, I need to cum” 

“Not yet, baby. Be a good boy” 

Castiel started to cry. It felt so good to take their relationship up to the next level. Dean could feel himself starting to let go. He was grunting and he pulled out of Castiel’s ass. Castiel let out a whimper at the loss.

Dean had Castiel lie down on his back. Dean stroked Castiel’s hair. 

“Open your mouth like a good boy” Castiel did and Dean started to fuck his face.

Dean grunted and moving faster. He reached down with his other hand and started to stroke Castiel. When Castiel was close. Dean stilled his hand and shot cum down Castiel’s throat, followed by urine. Castiel gagged, but drank it down. When he licked Dean’s tip, Dean gave a final squeeze and Castiel came. 

“Good boy” Dean soothed as Castiel cried. “Good boy. I’m going to clean us up.” Castiel just nodded.

Dean grabbed a warm cloth and came back, wiping Castiel carefully. 

“Did-did I do good, sir?” Castiel whispered.

“Yeah, baby. You were so good for me. Such a good boy.” Dean wiped himself and grabbed the cock cage. “I’m going to put this back on you.” 

“Wi-with the sound?” 

“Yes. With the sound.” Dean nodded.

Once the cock cage and sound were secured. Dean had Castiel sit under the table and warm his cock. The phone rang.

“Hey, Sammy. Yeah, my boy was so good” Dean cooed, stroking Castiel’s head. “Good. Good. Yeah. Grab some food for us. Thank you.” Dean hung up and looked at Castiel. “You’re so good to me baby.”


	9. Chapter 9

When Sam walked in with the food, Castiel was still under the table, warming Dean’s cock.

“How’d it go?” Dean asked Sam.

“She opened up more about what she saw.” Sam said. 

“Good. Baby boy, the food is here.” Dean rubbed Castiel’s head.

Castiel crawled from out under the table. He sat on the chair and Dean helped Sam hand out the food. Sam sat at the table and Dean raised an eyebrow. Sam blushed.

“Do you want to finish your lunch first?” Dean asked and Sam nodded. “Okay.”

Once everyone ate, Castiel tapped Dean’s arm.

“Sir. I have to pee.” Dean kissed Castiel and grabbed gloves, and going to the bathroom.

Sam took this time to clean up. He then went and got undressed, when Dean and Castiel came back out, Dean looked at Sam and smiled.

“I want to be pretty” Sam whispered.

“Okay, princess. Let me get my good boy all set up with some research and I’ll help you.”

“I would like the sound in. Please, daddy.” Dean nodded.

“Need you to go to the bathroom first, sweetheart.” 

Sam nodded and went to the bathroom. Castiel sat at the table and Dean stroked his cheek. 

“Once my pretty princess is ready, you’re going back to warming my cock and being my urinal. That is your sole purpose for the rest of the day.”

“Yes, sir.” Castiel whispered. Dean kissed him. “Sir, I have a question.”

“Yes?” 

“What…what if…my legs start to cramp?”

“You tap my ankle. You tap and you get a five minute break.”

“Thank you, sir.” Sam walked out.

“I’m ready, daddy.”

“Good girl.” Dean smiled as Sam went to the bed and lay down. 

Dean soothed Sam as he slid the sound in. Then Dean worked the bigger plug into Sam. Sam stood up and got in his panties, stockings and heels. 

“Such a pretty girl.” Sam got on his knees.

“Please. Paint my face like last night, daddy. Put my hair in ribbons again. I want to be so pretty. I want to be your good girl.” Dean ran his hand through Sam’s hair. 

“Yeah, you liked that princess?” Sam nodded. 

Once Sam was all dolled up, Dean sat back in the chair.

“Baby boy, you know your place.” Castiel smiled and got under the table. “Princess, dance for daddy” Dean instructed and Sam did. 

Later that night, Sam was sitting on Dean’s lap, staddleing him, being careful not to hit Castiel who still had Dean’s cock in his mouth. Dean ran his thumb over Sam’s nipple and he moaned a bit.

“You like that?” Dean whispered.

“Yes, daddy.” 

“Do you want to be a real pretty princess, Sammy?” 

“How?” 

“Baby boy, you may go have a stretch.” Castiel got out from under the table. “I’ve had this idea for a bit. If you say no, I completely understand” he spoke quietly. 

“What is it, daddy?” Sam sat back and Dean cupped his cheeks.

“Well, it’s messed up, sweetheart” 

“This whole thing is messed up” Castiel snorted and both men looked at him.

“Sorry, sir” he quickly responded.

“Princess, daddy was thinking of buying nipple pumps and pumping them up a bit. Like…” Dean trailed off. This was fucked up. It was his brother after all. Sam placed his hands on his brothers cheeks and kissed him. 

“would you buy me a sheer bra too?” Dean smirked.

“Yes, princess.” 

“I will try anything for you, daddy.”

“If you don’t like it, that’s okay. It can be an occasional thing. Like if you need to feel extra pretty.” Sam hugged his brother tight.

“I love you, daddy. I love you so much” Dean wrapped his arms around his brother. 

“I love you too, princess. Now, can you be a good girl and dance for me. My boy was such a good boy for me today, that I need to massage him.”

Castiel perked up at that and smiled wide. Sam got off of Dean and started to dance. Dean had Castiel lie on his back and started with his legs.

**Notes for the Chapter:**

> Too far?


	10. Chapter 10

**Notes for the Chapter:**

> Umm...got a little carried away...so sorry.

When they finally got back to the bunker, Sam hadn’t been able to be a pretty princess for two whole days. Castiel on the other was very pleased to have been used. Dean had ordered a black sheer bra while they were on the hunt and nipple punps, so they were at bunker. 

Dean was putting the cockcage with sound in on Sam. He wasn’t dolled up just yet. Dean took the gloves off when the plug was settled nicely in Sam’s ass. Sam got dressed. Stockings, panties, heels and the gloves.

“Make me pretty, daddy” Sam said.

“Just a minute, sweetheart. Do you remember what we talked about?” Sam nodded. “I have the pumps and the bra. Do you want to be the most prettiest princess ever, Sammy?” Sam sank to his knees.

“Oh, daddy. Please! Please! Pump my nipples up. Make me so pretty. Put the bra on me. I want to be a pretty girl. I want to be a pretty princess. Daddy, I want to be a good girl for you. Please!”

“On the bed, pretty girl.” Dean soothed.

Sam got on the bed and Dean picked up one nipple pump. He brushed a thumb over his brothers nipple before placing the pump and twisting it.

“Hn. Hn. Hn.” Sam gripped the sheets. 

“Aw, daddy’s sorry, princess. You’re doing so well. Do you want daddy to stop?”

“N-no. Make me pretty” Sam said.

Dean added the second pump. He smiled down at Sam, stroking his cheek. While Sam lay there, Dean did his makeup. The whole nine. When he was done he had Sam sit up and he did his hair. Dean looked at Sam, holding the ribbons.

“Oh yes, daddy. The ribbons, please!” 

“Okay, sweetheart” Dean cooed, placing the ribbons on.

When he was done, he laid Sam back down and pulled the pumps off. Dean licked his lip, looking at his brothers erect nipples. Sam stood up and walked to the mirror. Dean came up with the bra and placed it on. Sam let out a whimper when the sheer bra brushed against his sensitive nipples. Sam blushed and Dean cupped his cheek.

“Do you like it princess?” 

“Yes, daddy.”

“Yeah, daddy’s princess has pretty titties.” Sam blushed.

“I’m a pretty girl with tittes” Sam whispered. Dean kissed the side of Sam’s head. 

“Let’s show, Castiel.” 

Dean held Sam’s hand. They walked to the library and Castiel looked up, smiling.

“Baby girl. You just keep getting prettier and prettier.” Sam blushed and got on his knees

“Hold me, daddy? Hold me and tell me how pretty I am.”

“Of course.” Dean smiled and Castiel did too.

Dean sat on a chair and Sam sat on his lap. He rested his head on Dean’s shoulder and Dean held him tight.

“You are such a beautiful girl, Sammy. So pretty with your face all dolled up. Your ribbons in your hair. You have beautiful little tittes. Just so perfect. You are the prettiest girl in the whole wide world. Such a pretty princess. You’re a good girl, Sammy. A very good girl. That sheer bra with your erect nipples makes you even more beautiful. I love holding my pretty girl and making her feel safe and loved. Daddy loves his pretty girl.” Dean whispered. “I would do anything for my pretty girl.”

“Really, daddy?” Sam asked and Dean kissed the top his head.

“Is there something you’d like to share, sweetie?” Castiel asked.

“Yes, Castiel.” 

Sam got off of Dean and back on the floor.

“Please. Let me be a good girl, a pretty girl for a whole month. Lock my cock in a cage, keep the plug in me. Do my hair, makeup. Let me have pretty titties. I want to be a good girl, a pretty princess for a whole month. Castiel, daddy. Please! Oh, please!” Sam started weeping and Dean got on the ground and pulled his brother close.

Dean’s childhood was hard, but nothing like Sam’s. John constantly screamed at him, called him stupid and dumb. Told him he couldn’t do anything right. Called him a sissy and a disappointment. 

All Dean wanted to do was make his brother feel safe and loved. He knew Sam was broken, but he didn’t know how much until now. Dean couldn’t hold back his tears as he held his brother in his arms. Castiel got on the ground with some water whenever Sam was ready. 

“I ne-nee-need to be ta-taken care of, da-daddy. Pl-please, ta-take care o-of me” Sam sobbed.

“Sweetheart, I’m going to take care of you. I’m going to make sure you are the prettiest princess. I promise.” Dean said.


	11. Chapter 11

That night the boys got Sam into a nice warm bath. Castiel and Dean were washing him, slowly. Dean kissed the side of his head.

“We’re going to shave you, pretty girl. Get you all nice and smooth.” Dean whispered.

“Like a real girl” Sam whispered.

“You are a real girl, sweetie” Castiel soothed.

“We’re going to wash your hair too, get it in curlers” 

Castiel washed Sam’s hair, massaging it and earning a moan from him. He then took the foam rollers and curled Sam’s hair. They made sure the bathroom was nice and Warm. They helped Sam up, happy that they got heated floors and he helped Sam down.

“Okay, princess, daddy’s going to shave your chest now.” Dean whispered.

“Thank you, daddy” Sam smiled.

Dean put gloves on and so did Castiel. Dean sprayed the cream and rubbed it on Sam’s chest. He dipped the razor in the water and started to shave him.

“Castiel, are you going to lock my cock away.” Sam asked.

“Not right now, baby girl. We need to shave you there too.” Castiel soothed, garbbing the lotion to rub on Sam when Dean was finished cleaning.

Once Dean was done, he Sam on his lips and moved between his legs. Castiel got a cloth damp and wiped off all the extra cream and hair. He grabbed the lotion and rubbed it on Sam’s chest.

“Going to do your legs, now sweetheart.” Dean informed him. When he was done, he changed his gloves and stroked the younger man’s cock. “I need you to be a good girl and stay very still for daddy”

“Okay.” he whimpered.

When Sam was fully shaved, Castiel rubbed the cream on while Dean cleaned up. 

“You were so good for us, sweetie. So, good. You look really pretty.” Castiel said, rubbing the cream on Sam’s private area. 

“Thank you, Castiel.”

Dean and Castiel helped Sam up. They brought him to a full length mirror and he gasped, smiling.

“I’m all smooth.”

“Yes, you are pretty princess. Now, time to get you to bed.” 

“Daddy wont have you in the sound tonight. That will be tomorrow once you go pee.” Castiel said grabbing Sam’s nightwear.

Once Sam had his cage, stockings, panties and nightgown. Dean sat Sam down and grabbed a scarf.

“What’s that for, daddy?”

“Need to make sure that your hair stays all nice.” He said wrapping the scarf and tying it. 

“Now, daddy and I are going to play for a bit. You just rest sweetie.”

“Yes, Castiel.”

“Be a good boy and go to the spare room, get undressed and wait for me.” Dean instructed Castiel.

“Yes, sir.” Castiel kissed Sam and left. Dean started to get changed in dress pants, dress shirt, sleeves rolled up and he grabbed latex gloves.

“Daddy, I love you.” Sam spoke quietly.

“Daddy loves you too, princess.”

“What are you doing to do to your good boy?” Dean sat on the bed and smiled a bit, stroking Sam’s cheek.

“I’m going to eat him out and then see how many fingers I can get in his ass.” Sam gasped quietly.

“oh, my.”

“Mmm hmm. Now, be a good girl and get some rest” Dean kissed Sam.

“Goodnight, daddy” 

“Goodnight, pretty girl.”

Dean entered the room and pulled the latex gloves on, making Castiel’s cock twitch. 

“Are you going to be a good boy for me?” Dean asked.

“Yes, sir. I’m going to be a very good boy.” Castiel replied.

“On your elbows and knees, baby” 

Castiel did quickly and Dean grabbed the lube. Dean spread Castiel’s cheeks and licked. Castiel’s hips bucked and Dean spanked his ass.

“Sorry sir” 

Dean eat Castiel out, Castiel was growing harder and harder. Dean pulled his mouth away. Dean rubbed Sam’s hole. He grabbed the lube and rubbed it on one finger and pushed in, opening him up.

“Nnn. Siiiiiir” Castiel whined. 

“Are you going to relax for me? Are you going to show me how you’re a good boy and see how many fingers I can get in?”

“Ye-yes sir.” Castiel whimpered.

Dean slipped two fingers and rubbed Castiel’s prostate. Pre-cum leaking from Castiel’s cock. Finally Dean slipped the third finger in.

“Mmm. What are you thinning about, baby boy?

“Ho-how thi-this feels good. Ho-how I-Want your cock. Th-that Sammy lo-looks so-so pretty.”

“Yeah, our girl is very pretty.” Dean smiled

Dean pulled his fingers out and squirted more lube and then slowly worked three fingers and started to add his pinky.

“You relax, baby. Thank about Sammy and how our girl is going to look so pretty tomorrow. There, that’s it. Good boy. Good boy. Deanslid four fingers in.”

“Sir” Castiel whimpered. “Sir, you’re not going to…”

“No. I’m not going to fist you, just wanted to see if I could do this. I’m not going to fist you, baby boy.” Dean pulls his pinky out and the other three fingers.

“Sir, please. Please. I want skin to skin. Touch me with your hand. Please!” Castiel begged.

“Yeah? You want that baby?”

“Yes, sir.”

Dean reached down and pumped Castiel’s cock with the gloved hand.

“You want my skin, baby boy? You think you’re a good boy who has earned that?”

“Yes!” Castiel whimpered.

Dean took one glove off and inserted two gloved fingers in his ass, hitting his prostate and started to pump Castiel with his ungloved hand.

“Mmm, like that baby? You like skin to skin.”

“Yes, sir. Sir, it feels-OH!” he cried out.

“Yeah, you want to cum, baby boy? You want to cum for me.”

“Mmmhmm” He nodded. Dean rubbed harder in Castiel and he came spilling out.

“There’s a good boy.”


	12. Chapter 12

In the morning Dean kissed Sam and woke him up. Sam got out of his nightwear and went to the bathroom, while Dean got dressed. He let Castiel sleep in a little longer since last night. Dean grabbed Sam’s stuff and brought it to the spare bedroom. Sam followed close behind.

“Daddy?” Sam asked walking in naked.

“My good boy needs some sleep. So, daddy is going to get his girl all pretty in here.” Sam smiled and laid down on the bed. Hair still in the scarf. “Going to start with your titties, get those nice and pumped up.” Dean pulled on gloves

“Yes, daddy” Sam whimpered, closing his eyes when Dean brushed a thumb over it. 

Sam whimpered when Dean started to pump up the right nipple. Dean pumped up the left one and moved between Sam’s legs. He ran his gloved hand over Sam’s smoothed legs.

“You look so pretty all bare like this” Dean said.

He grabbed the cock cage and lube. He lubed Sam’s tip and placed the cage on. Dean grabbed the sound and lubed it, slowly inserting in, screwing the ball on. 

“Need you to spread your legs pretty girl. Daddy’s going to put your plug in.”

“Is it the bigger one, daddy?”

“Yes princess, it’s the bigger one.” 

Once Sam’s plug was secured, Dean took the gloves off and pulled Sam’s panties up.

“Let me, daddy” Sam said.

“No sweetheart. Let daddy dress you.” 

Dean placed the fishnet stockings and heels on next. He walked over and stroked Sam’s cheek. Sam smiled. Dean pulled the gloves on Sam’s arms.

“I’m feeling pretty already” Sam whispered.

“Good girl. Now, let’s get the pumps off” 

Dean pulled them off with a pop and Sam sat up. Dean placed the sheer bra on. He led Sam to the table and took the scarf off and did Sam’s make up. 

“I bought you sparkly eye shadow, princess.” Dean smiled, putting it on.

“Thank you, daddy”

When Sam’s makeup was done, Dean started taking the curlers out. He helped Sam stand up and walked him to the mirror.

“My hair is so pretty, so curly. Oh, daddy. Thank you. I’m a pretty girl.

“Daddy’s going to put your hair up. Not in pigtails, some up and some down, so we can see your pretty curls.

“With the ribbons?” 

“Of course” Dean kissed Sam’s lips. Once the ribbon was in, Dean and Sam went to wake Castiel up. Castiel smiled looking at Sam. This was the happiest he had seen him. 

“Baby girl, you are breath taking.”

“Thank you, Castiel.” 

“Thank you for letting me sleep in” he said to Dean.

“You deserved it, baby.” Dean smiled. He crawled into bed and pulled his pants. Need to pee” Castiel nodded and wrapped his mouth around Dean. “Dance for me princess. Tell me how you feel.” Sam started to dance.

“I feel like the prettiest princess in the whole wide world. My tittes a perfect. I love my curly hair and…and being shaved. Daddy you made me feel like a real girl. Made me feel safe. Castiel makes me happy. I feel so beautiful.” He said running a hand over his neck. 

“Yes, baby girl. You are beautiful.” Castiel said, snuggling up to Dean when he was done.

**Notes for the Chapter:**

> I had this idea...of Sam maybe calling Castiel mommy...I don't know.


	13. Chapter 13

Castiel was in the kitchen making lunch and Dean was doing research in the library. 

“Daddy” Sam asked batting his eye lashes and swaying his hips side to side.

“Do you have to pee, princess?”

“No, daddy. I thought about what I wanted to call Castiel, but I’m not sure.”

“Come here, sweetheart. Sit on my lap and tell me.” Sam walked over and sat on his brothers lap. Dean rubbed a hand on his back. “Come on, pretty girl. What’s on your mind?”

“It’s dumb.” Sam said quietly. 

“Shhh. Don’t say that.” 

“I want to-to call him…he might not like it. He wont like” Dean pulled him tight to him.

“We want you to be safe, we want you to be loved. You’re a good girl. If it’s to help you cope, we will do it. Just tell daddy.”

“I-I want to call him…mommy” Dean kissed the side of Sam’s head.

“Yeah? You want to call him mommy? Does my pretty girl, want a mommy and a daddy?”

“Yes, but he’s not a girl. He wont like that at all.”

“Don’t say that. Do you want me to speak to him? I can do that, princess.” 

“Yes, daddy.”

“Is there anything else, sweetheart?” Sam blushed.

“What is it?”

“I-I would like to talk to Castiel first.”

“Let me talk to him first, can you be a good girl and do some research?”

“Yes, daddy” 

Dean walked into the kitchen and wrapped his arms around his waist and kissed the back of his neck.

“Hey, baby.” Dean whispered.

“Hey handsome.” Castiel smiled.

“Our girl spoke to me. She wants to call you something, but is a bit nervous about it.” Castiel turned to face Dean.

“What is it?” Dean cupped his cheek.

“Sammy wanted to call you mommy. She knows it’s strange and you’re not a girl, but-“ Castiel kissed Dean.

“If that’s what my baby girl wants, that’s what my baby girl can do.” 

“Yeah?” 

“Yes.” Castiel smiled.

“You are an amazing boyfriend, you know that? How did I get so lucky?” Dean asked. This time it was Castiel who held Dean.

“You are an incredible boyfriend and an amazing brother. The world is a better place because of you. You make everyone happy. Are you happy?”

“Yeah, baby. I am. You make me so happy” Dean whispered. Castiel kissed the top of his head.

“Remember that this is a two way street. You take care of us. Let us take care of you sometimes.”

“This is perfect, Cas. Just you holding me. You gotta talk to our girl” Castiel kissed Dean’s lips.

“Once I talk to our pretty girl, can I hold you?” Castiel whispered.

“Yeah, baby. I would love that.”

Sam was sitting at the table and Castiel walked in, placing his hands on Sam’s shoulders.

“Baby girl, daddy spoke to me” Castiel spoke gently.

“He-he did?” Sam whimpered. Castiel had Sam sit on his lap.

“Sweetie, you want to call me mommy?” Sam nodded. “Yeah, you would like that? Because if that makes you happy, baby girl, you can call me mommy. It would make me happy.” Sam looked up at the blue eyed man.

“Really?” 

“Yes, sweetie. Really.” Sam got off of Castiel’s lap and knelt at his feet.

“Please. Be my mommy. Take care of me. I want to be mommy’s baby girl”

“You are. You are, mommy’s baby girl” 

“Mommy?” Sam asked.

“Yes, baby” Castiel smiled.

“I want-I want something to be called by a different name. Only this month though as I’m a full on pretty girl”

“What would you like?”

“For my ass to be called a pussy.” Sam looked down. “I want daddy and mommy to fill it up and plug it.”

“Baby girl, we can do that, but you need to ask daddy.” Sam nodded. Just then Dean walked in.

“Daddy?” Sam whispered.

“What is it princess?”

“Ca-Can for this month, you call my ass a pussy?”

“Yes, pretty girl.”

“Tell daddy what else.” Castiel coaxed and Sam blushed. “Be a good girl for mommy”

“I want daddy and mommy to fill my pussy with their cum and plug me.”

“Whatever my sweetheart wants.” Dean said crouching down and cupping Sam’s cheek.

**Notes for the Chapter:**

> Noooow...I may have gone to far. 
> 
> Anyway. I'm thinking of adding a fourth part to the series...what do you you think? Maybe mommy and daddy's pretty girl needs to be a pretty baby for a while? diapers and all? What do you think?


	14. Chapter 14

Sam was all dolled up, hair curled. He was dancing for his daddy and mommy, while daddy was four fingers deep in mommy’s ass.

“Nnn.” Castiel whined. He was spreading his ass for Dean.

“Shhh. Baby, relax for me. Relax. I’m going to take care of you.” Dean soothed.

“Are you okay, mommy?” Sam asked.

“Ye-yes, bab-baby girl” Castiel gritted out.

“You like this, baby? You like how our pretty girl is watching?” Dean whispered.

“Mmph” Castiel moved to grip the sheets.

Dean pulled his fingers out and added a lot do lube. Castiel took slow deep breaths and Sam watched in awe as Dean got his whole fist in Castiel’s ass.

“Soo good, baby boy. Sooo good for me.” Castiel was crying. It didn’t hurt, but an experience he hadn’t sensed before. “Princess, once daddy is done with his good boy, he’s going to fill up your pretty pussy.”

“And mommy?” Sam asked hopeful. “Is mommy going to fill up my pussy?”

“Not tonight, mommy needs his rest. Lots of fluids. In the morning though.”

Dean slowly pulled out of Castiel and he rubbed a hand on the older man’s back. He took the gloves off and carefully cleaned Castiel.

“Sweetheart, please hold mommy for a moment.” Dean instructed.

Sam got on the bed and held a crying Castiel. Dean went a grabbed water for Castiel. He debated grabbing the urine, but not after finally getting his fist in him.

“I’m here, mommy. I’m here.” Sam said.

“Than-thank you, baby girl” 

Dean walked in with Water and a straw. He climbed into bed with Castiel and held the water up for him to drink. Fifteen minutes later, Castiel was starting to get a little sleepy.

“Dean, play with Sammy’s pretty pussy.” Castiel whispered.

“Okay. Come on, pretty girl. You go get ready for bed, get in your pretty nightgown and when you’re done, daddy will be ready.”

“Yes daddy” 

Sam grabbed his things and went to the bathroom. Dean peppered Castiel’s face with kisses

“How are you, baby? Did I hurt you?”

“No, Dean. That was very pleasurable.”

“You didn’t come, are you okay with that?”

“Yes, Dean. Besides, I need to be good to fill my baby girl’s pretty pussy.” Dean kissed Castiel and got up. 

Dean pulled his pants off, put gloves on and started to stroke himself. Sam came out without panties on. He got on the bed and Dean came over, pulling the plug out. Castiel went to wash it, even though Dean told him not too.

“Mmm, princess, your pussy is very pretty.” Dean said pouring lube on Sam’s hole. 

“Thank you, daddy” Sam whimpered.

“Did you like watching me play with mommy?” Dean worked two fingers into Sam and a third.

“I did. Oh, daddy I loved it so much. Would you fist my pussy?” 

“No, sweetheart. Daddy will never be doing that to you. Understand?”

“Yes, daddy” 

“Get ready, pretty girl. I’m going to fill your pussy.”

Dean slid into Sam and started to move slowly. Sam rocked back. Dean started to moan. Castiel was back in bed, smiling at the loves of his life.

“Mmm, your pussy feels so good, princess” 

“Daddy, I love having my pussy full. Oh it makes me feel pretty”

A few minutes later Dean came in Sam and he pulled out, plugging him up. Dean rolled Sam over. He changed his gloves and took the sound out of the cock cage. Dean pulled Sam’s panties up. He took the gloves off, cleaned himself and climb into bed, sandwiching Sam between mommy and daddy. 

“You’re a good girl for me Sammy. Such a good girl.” Dean cooed rubbing a hand on his arm.


	15. Chapter 15

“Daddy, what’s this?” Sam asked holding up a package.

“That’s something for you mommy” Dean smiled.

“Oh. Good. He’ll like it when he comes back.” 

“Mmm hmm.” Dean smiled.

“Alright princess, daddy needs to do some research.”

“I need to pee.” Sam looked down and Dean smiled. 

He and Sam went to the bathroom. Dean slipped gloves on and pulled Sam’s panties down and took the sound out and the cage off. Sam went to the bathroom and Dean wiped him. With his gloved hand he stroked Sam’s cock. It twitched and Sam looked at Dean.

“Daddy is very pleased with how responsive this is getting. Good girl” 

“Thank you, daddy” Sam smiled.

Dean had Sam sit on the toilet and he placed the cage and sound back on. Dean took his gloves off and looked at Sam’s pumped nipples in the bra. Dean leaned forward and kissed Sam’s neck, bring his hand to Sam’s nipple and started to roll it.

“Such pretty tittes, sweetheart.” He murmured against Sam’s neck. 

“Than-thank you.” Sam breathed out. Dean helped Sam stand up and pulled his panties back up. 

“Pretty girl, daddy is going to give you a spanking before he works. Grabbed Dean’s hands.

“Oh yes. Please.” 

Once Sam got his praised spanking he went and danced for Dean. Later on Sam did some research and Castiel came home.

“Mommy, daddy bought you a gift!” Sam smiled.

“He did? That’s very nice, baby girl” Castiel said placing a kiss on his lips.

Dean and Castiel excused themselves and Castiel opened the gift. He gasped and groaned a bit.

“You like it, baby?” Dean asked.

“Yes.” Castiel said. 

He held this cock cage that had a tube attached to it and a butt plug. So if Castiel started peeing, his own piss would go in his ass. 

“Good. I’m glad.” 

“Sir. This is amazing.” Castiel said kissing Dean.

“Mmm, you’re amazing.” Dean whispered. Dean unzipped his pants. “I’ve been holding it for a while, open your mouth.” 

Castiel got on the ground, wrapped his mouth around Dean and drank his piss. When he was done, licked the tip and Dean did his pants up. 

“Such a good boy”

Dean and Castiel walked in and Sam was on his knees waiting for them to come back.

“Sweetie?” Castiel asked.

“Please. I want daddy to fist my pretty pussy.” Dean and Castiel’s eyes softened. Dean shook his head and crouched down in front.

“Princess, daddy already told you. Your pretty pussy is not for fisting.”

“But you gave me a bigger plug” he said looking at Dean.

“I know, princess. We want to stretch you a bit, but we’re sorry. You’re too fragile for that.” Dean placed a kiss on Sam’s lips.

“Okay, daddy” Sam smiled.

**Notes for the Chapter:**

> I'm working on the pretty baby Sammy story. I might do one or two more of this and finish it before moving on.   
> Anything you want to see. Or anything you ant Sammy to call something?


	16. Chapter 16

Dean had Sam on his elbows and knees, butt plug out. Dean put latex gloves on and grabbed the razor.

“Going to shave you princess.” Dean soothed.

“Daddy shaving my pussy?” Sam asked.

“Yes. Then my pretty girl is going to get an enema” 

Once Sam was shaved, Dean filled up the bag and gave Sam an enema. 

“What’s going on?” Sam asked.

“Mommy is going to eat your pussy.”

“Really” Sam squeaked in excitement.

“Uh huh.” Dean shut the water off and started to massage Sam’s stomach.

“Nnn, it hurts” he whined.

“I know, pretty girl. I’m sorry” 

When Sam released, Dean too the cage off of Sam and had him get changed into his nightgown without panties. 

Dean started making out with Castiel. Dean had pumped Sam’s nipples up some more for this. The boys asked him to lay on his back, legs spread. Dean moved to be beside Sam, putting on gloves and Castiel positioned himself between Sam’s legs. He pulled on latex gloves and spread Sam’s cheeks.

“Mmm, baby girl, you have a pretty pussy. Mommy likes it.” Castiel whispered. He wiggled his tongue on Sam’s hole.

“AH! Mommy!” Sam cried out. Dean rubbed a hand on Sam’s forehead and kissed his lips.

“Deep breaths.” Dean murmured against Sam’s lips.

Castiel continued to lick Sam’s hole. Dean kissed down Sam’s neck and his hand moved the baby doll dress and placed a kiss on Sam’s pumped nipple. One hand stroking his hair and the other stroking Sam’s cock.

“Da-da-daddy” Sam whimpered. 

“You like that princess. You like when daddy sucks on your tittes.” 

“Mm hmm” Sam closed his eyes. 

“You have such a pretty pussy.” Castile said. He sucked on his gloved him and then rubbed it against Sam’s hole and slid it in.

Dean felt Sam getting hard. He lightly bit Sam’s nipple. Castiel pulled his finger out and stuck his tongue in Sam’s ass. Dean went back to kissing up Sam’s neck.

“What a good princess you are. You like it? You like mommy licking your pussy? You like daddy playing with you? your titties. You’re so beautiful sweetheart. Daddy and mommy are going to take good care fo their girl. That’s you, Sammy. You’re our girl”

“I wanna cum, daddy.” Sam whimpered.

Dean sat up and used both hands on Sam’s cock, brushing his thumb over Sam’s tip. Castiel slid two fingers inside of Sam’s ass and hit is prostate. Sam was panting, gripping the sheets. Dean squeezed Sam’s balls, rolling them.

“Please! Please! Oh, please! Mommy, that feels sooo good. Daddy, I need it!”

“I can feel you clenching baby girl” Castiel cooed. Dean moved his hand faster on Sam’s cock. 

“You going to cum, princess? You going to cum like a good girl?” Dean asked. 

“Ye-ye-yes” Sam grunted.

“Okay, sweetheart. Sum for daddy” 

Castiel hit the right spot and cum went over Dean’s gloved hands and Sam was panting, crying a bit. Both of them took their gloves off. Dean went over to Sam’s face and kissed his lips, stroking his forehead . 

“You were such a good girl for us. So pretty, so beautiful.” Dean praised. He placed kisses to Sam’s forehead and Castiel went to grab a cloth and cleaned Sam up. 

“Baby girl, that was wonderful” Castiel whispered.

“Thank you, mommy.”


	17. Chapter 17

**Notes for the Chapter:**

> Last chapter, hope you like.

In the morning, Dean kissed Castiel. Castiel was holding their princess.

“We’re going to fill up our girl’s pussy and then you’re going to be a good boy for me and use your new toy.” Dean whispered in Castiel’s ear.

“Yes sir” Castiel mumbled. 

“Good, now time for the bathroom”

Castiel got out of bed. Dean sat up and Castiel sank to his knees and Sam told over.

“Mommy?” he whimpered. Dean placed a hand on Sam’s cheek

“Princess, daddy is using mommy right now, then we’re both going to fill your pretty pussy this morning before he becomes my good boy.”

“Okay daddy” Sam mumbled still sleepy. 

Dean had Sam get dressed for the morning. Both men helped him. When he was all dolled up, hair curled and in ribbons, face painted, nipples pumped he went to the bed on his elbows and knees.

“No, princess, we need to put your cage on.” Dean said holding the cage in latex gloved hands.

“Sorry, daddy” Sam said rolling on his back. 

“Yeah, going to lock up you clit, aren’t we pretty girl” Dean said. Sam had asked them to call his cock a clit as well and they loved it. 

“Yes, daddy. With the sound?” 

“Uh huh. Then mommy is going to fill you up first.” Dean said lubing Sam’s tip and sliding the sound in and locking it on the cage. “Now, show us your pussy” 

Sam rolled over and stepped aside and Castiel had put gloves on. He squirted some lube on Sam’s hole and started to rub it.

“Okay, baby girl. Going to get you nice and prepared.”

“Yes mommy” Sam whispered.

When Sam was open Castiel slid in and Sam started to rock his hips. Castiel moved faster and finally came in Sam. He slipped out and Dean slipped in. When he came in Sam, he reached over and plugged Sam’s ass.

“There we go princess” Dean said.

Castiel had left to give himself and enema and Dean put Sam’s panties on him. Sam reached his arms up and Dean lifted his girl in his arms.

“You were a good girl for us. Such a good girl.”

“Thank you for fucking my pussy, daddy.” Sam whispered.

“You’re welcome sweetheart.” 

Dean put Sam down and told him to do some research. Dean walked into the bathroom and gave Castiel a second enema. He then slipped gloves on and kissed him.

“Are you ready to be a good boy?” he asked.

“Yes sir.”

Dean placed the butt plug on first and then took off Castiel’s old cock cage and placed it with this and then placed the tubing on the butt plug. Dean took the gloves off.

“You’ll be drinking my piss, not yours. Just want to see how full we can get you of your own piss.” 

“Yes sir.” 

“Good boy.” Dean kissed Castiel.

Dean and Castiel walked to the library where Sam was. Dean still naked sat down on the chair.

“Princess, daddy’s good boy is going to warm his cock. Can you be a good girl and dance for daddy?”

“Oh yes!” Sam squealed. 

Sam started to dance and moaned a little. A little while later Castiel tapped Dean’s ankle and crawled out.

“You were good baby boy.” Dean praised. 

Castiel stood there blushing and then peed. He whimpered feeling his own ass get filled with his piss. Dean stood up and cupped his cheek, kissing him lightly. 

“Does that feel good?” he whispered.

“Yes sir.” Castiel breathed out.

“Are you full?” he shook his head. “Good job, baby.” 

Five minutes later Castiel was under the table again warming Dean. Sam got on the ground.

“Oh daddy, please! Please! Play with my titties and clit. Let me be a good girl for you. I want you to show me how pretty you think I am.” Dean smirked.

“Yeah, you want that princess?” Sam nodded smiling. 

“Once my good boy gets his ass nice and full, then daddy will play with your pretty titties and clit.” He said stroking Castiel’s hair.

Mid afternoon Castiel was full and started tearing up. Dean walked over and placed a kiss on his lips.

“Is my little piss boy full?” he whispered in Castiel’s ear nipping at it.

“Mm hmm” Castiel nodded.

“Can’t hold anymore?” Castiel shook his head. “Maybe sir should fist you again, get you nice and stretched too.”

“Please” Castiel whimpered.

Dean nodded and led Castiel to the bathroom. He turned on the shower and put gloves on. He pulled the plug out and Watched as Castiel’s urine rushed out of his ass. Dean took the cage off and put new gloves of. He washed Castiel out thoroughly. 

When Castiel got out, Dean took the girls off and kissed him. 

“You were so good baby.” Dean whispered.

“Thank you sir.” Dean pulled him into a hug and stroked his hair.

“I’m going to play with our girl. Want to join?” 

“No, you go play with daddy’s good girl.” Castiel smirked. Dean kissed him.

“Did you like that?” 

“Oh yes, Dean. I did.” 

“Good.”

Dean walked into the living room and saw Sam sitting and reading. Dean cleared his throat and Sam looked up.

“Daddy?” Sam asked.

“Come on, princess. Daddy’s going to play with his pretty girl.” 

Dean got Sam’s cage off, put kept the panties on and laid him gently on the bed. He pulled on a glove and started to kiss Sam. Dean kissed down Sam’s neck and slid his hand down Sam’s panties.

“Mmm. You’re beautiful” Dean whispered against Sam’s neck. “You like this?”

“Yes daddy” Sam breathed. “Ho-how come daddy uses the glove?” 

“Well, princess.” Dean placed a kiss on his chest. “Daddy likes latex gloves. He likes the feel. Do you?”

“Yes” Sam let out a moan when moved the sheer bra aside and sucked on Sam’s nipple. “Mmm, daddy. Feeeels soooo good. Stroke my clit, daddy.” Dean started to moved his hand and sucked, biting lightly.

“You feel so good princess. Such a good girl for daddy” Dean said before switching to the other nipple. “You like having our cum in your pretty pussy?”

“Ye-yes, daddy. I love it so much.”

“Good girl.”Dean pulled Sam’s cock out of his panties and stroked him. “Be a good girl and play with your titties Dean said.

Dean played with Sam’s cock. Sam took his right hand and ran it across his chest, shuddering at the satin eel of the gloves. He took his left hand and ran it down his cheek. His lips parted lips when he tweaked his nipple. 

“Mmm, daddy, your pretty princess loves this.”

That night Dean got his subs ready and they went to bed. Castiel woke up when he felt the bed was wet. Dean got up too and turned on the light. It was Sam. He was curled up in a ball and crying.

“I’m sorry. Daddy, mommy, I’m sorry. I’m sorry.” 

“It’s okay princess.” Dean soothed. 

“Come on, baby girl, let’s get you cleaned up.” Castiel whispered.

Dean lifted Sam in his arms and carried him to the bathroom while Castiel cleaned up the sheets.

**Notes for the Chapter:**

> Now...pretty baby Sammy.
> 
> Let me know what you want to see.


End file.
